Trade in Skyrim is oversimplified and uninteresting. A particular type of merchant always has the same amount of gold and offers you the exact same prices as the same type of merchant in another part of the country. Merchants in small towns differ very little from those in the larger cities, and the only factors that affect price are your speech skill and any barter enchantments you might have.

Bartering does have its limitations. Many bigger (i.e., chain) businesses will not entertain the idea and even smaller organizations may limit the amount of goods or services for which they will barter (i.e., they may not agree to a 100% barter arrangement and instead require that you make at least partial payment). But in an economic crunch, bartering can be a great way to get the goods and services you need without having to pull money out of your pocket.
Throughout the 18th century, retailers began to abandon the prevailing system of bartering. Retailers operating out of the Palais complex in Paris, France were among the first in Europe to abandon the bartering, and adopt fixed-prices thereby sparing their clientele the hassle of bartering. The Palais retailers stocked luxury goods that appealed to the wealthy elite and upper middle classes. Stores were fitted with long glass exterior windows which allowed the emerging middle-classes to window shop and indulge in fantasies, even when they may not have been able to afford the high retail prices. Thus, the Palais-Royal became one of the first examples of a new style of shopping arcade, which adopted the trappings of a sophisticated, modern shopping complex and also changed pricing structures, for both the aristocracy and the middle classes.[18]
And that means everything from tuna to stamps to cigarettes has its own unique value in a trade and barter market. — Alexandra Cardinale, Vox, "Why ramen is so valuable in prison," 14 Nov. 2018 European officials were also looking at a barter system that would allow Iran to sell oil, for example to China, and use the proceeds from that sale to purchase goods or technology from Europe. — Laurence Norman, WSJ, "Europe’s Payment Channel to Salvage Iran Deal Faces Limits," 25 Sep. 2018 With unemployment around 9 percent and consumer prices surging, some Argentines are again turning to barter clubs, which first emerged during the collapse nearly two decades ago. — Almudena Calatrava, Fox News, "Argentines seek soup kitchens, barter markets amid crisis," 10 Sep. 2018 This particular search insired Gellar and Laibow to hop on the phone and barter. — Colleen Leahey Mckeegan, Marie Claire, "Sarah Michelle Gellar's Second Act? Disrupting the Food Industry," 18 Apr. 2017 Choco Pies became so prevalent for sale or barter on the streets that North Korea reportedly banned their import to Kaesong in 2014. — Brian Murphy, Washington Post, "The Choco Pie dividend: South Korean firms are drooling at the prospect of business in the North," 17 June 2018 In 1996, amid crippling famine, Ji tried to steal a few pieces of coal from a rail yard to barter for food. — Brian Murphy, BostonGlobe.com, "Could these outspoken North Korean defectors return home?," 11 June 2018 In 1996, amid crippling famine, Ji tried to steal a few pieces of coal from a rail yard to barter for food. — Brian Murphy, BostonGlobe.com, "Could these outspoken North Korean defectors return home?," 11 June 2018 Instead, like many early civilizations, they were thought to mostly barter, trading items such as tobacco, maize, and clothing. — Joshua Rapp Learn, Science | AAAS, "The Maya civilization used chocolate as money," 27 June 2018

While there are most certainly safety considerations – and in some cases, a time commitment – bartering can be quite rewarding. You may not have a surplus of spendable money, but you do have talents, skills, and miscellaneous goods that are just as good as cash. With a little thought, and willingness to make the effort, you can use bartering to obtain the goods and services you want without impeding your cash flow.

Other countries, though, do not have the reporting requirement that the U.S. does concerning proceeds from barter transactions, but taxation is handled the same way as a cash transaction. If one barters for a profit, one pays the appropriate tax; if one generates a loss in the transaction, they have a loss. Bartering for business is also taxed accordingly as business income or business expense. Many barter exchanges require that one register as a business.